After his music career faded, the 56-year-old rapper, born Robert Matthew Van Winkle, found a new calling: real estate investment. The 90s sensation offers five tips to succeed as as an investor.

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Vanilla Ice is known to the world as a preeminent one-hit wonder, who remained a cultural figure long after his song — “Ice Ice Baby” — and the controversy it generated, faded from the dominant cultural milieu.

After his music career faded, the 56-year-old rapper, born Robert Matthew Van Winkle, found a new calling: real estate investment.

Van Winkle recently detailed how he built up a mini real estate empire and managed to elevate his net worth to $20 million decades after his single was charting in an appearance on the “Wild Ride” podcast of Jackass star Steve-O.

“I made millions for doing nothing!” Van Winkle told Steve-O during the appearance.

For those looking to follow a similar path the Iceman took, we’ve parsed a few key points from the interview to lay out Vanilla Ice’s investment strategy and philosophy.

1. Record a chart-topping song

You’ll need to start with some liquidity if you want to be a serious real estate investor, and a Billboard-topping certified gold single is a great way to get some pocket change and start scooping up houses. “Ice Ice Baby” sold an estimated 160 million-plus copies worldwide following its 1990 release — more than enough to buy a few houses.

“We were selling a million copies a day, easy,” Van Winkle told Steve-O.

2. Buy properties in a diverse range of markets

To hear Van Winkle tell it, he began his investment journey by buying up more houses than he could use “all over the country.” When he began to sell his properties off, he was surprised by how lucrative the sales were, he said on the podcast.

“They sold really quick and I made millions for doing nothing,” he said.  “I didn’t even change the carpet.”

3. Develop a game plan and a specialty 

Once Van Winkle caught the investing bug, he started increasing the number of homes he purchased and put more effort into renovating them. He also began to develop a game plan for the type of homes he purchased, and how he purchased them, telling Steve-O he prefers to buy properties off-market instead of from Multiple Listing Services and to buy distressed properties and tax liens, which he says gives him the chance to buy properties for “pennies on the dollar.”

4. Flex your construction and design muscles

The best investors are the ones who roll up to their properties in their own trucks with their own tools, and Vanilla Ice is no exception. Van Winkle told Steve-O his fascination in real estate was sparked when one of his homes was destroyed by Hurricane Andrew in 1992, and he decided to renovate it himself and sell it.

Van Winkle says he ended up going to design school and working as a general contractor for several years — skills that have undoubtedly given him a leg up in his career as a real estate investor.

“It’s fun swinging a hammer, man, and being one of the guys. Your workers look at you like you’re one of them,” Van Winkle told The New York Times in 2010

5. Build your brand through content

Even if he has shifted most of his efforts into real estate investment, Van Winkle is still an entertainer at heart. Cashing in on the popularity of real estate and renovation television shows, he turned his investment journey into a reality television show — The Vanilla Ice Project — on the DIY Network and it has run for nine seasons.

The show follows Van Winkle as he oversees his teams of contractors. The show has been so successful, that Van Winkle has launched a training course that aims to help others succeed in investing.

Email Ben Verde

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